100km of Chianti
Hiking Tour
Connect two medieval Tuscan cities with your own two feet!
This unparalled experience of the Chianti wine region begins in the heart of Florence. In the birthplace of the Renaissance, you will rest up and explore for a couple of days before embarking on the 100km expedition. With your guide, Emanuele, you will depart along the ancient Via Romea Sanese until reaching the medieval city Siena. Between the two cities you will take refuge in four unique points of restoration including the villages of San Donato in Poggio & Castellina in Chianti.
Highlights
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Spend two nights exploring Florence. Embark on a hike through the Chianti wine region and spend one night in Siena at the end of the road.
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Travel the ancient road connecting Florence and Siena, tracing the footsteps of millennia of travelers. Each leg of the journey will be guided by our Chianti expert and environmental guide, Emanuele.
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Endulge in trailside picnics memorable evening meals with tastings in the the best eateries and wineries of the region.
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Witness mind-blowing views of The Chianti and enjoy cherishable encounters with local foragers, shopkeepers, chefs, and more.
Included
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7 nights and 6 unique stays in charming Tuscan Hotels and Agritourisms.
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Private ground transportation as indicated in the itinerary and daily luggage transfers between hotels, while you trek.
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All breakfasts
Picnic lunches on walking days
5 group dinners
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Full time accompaniment & expertise provided by your guides, Andee & Emanuele
8 day guided hiking experience in Tuscany,
2 Winery Visits & Tastings
Registration
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Starting at $6,995 per person
$600 Single Supplement
Groups of 6 or more travelers
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May 4 - 11, 2025
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Send an email to andee@travelingnative.com to inquire about availability for your private group during the following time periods:
February - June
September - November
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Personalize your journey through the Chianti with add-on excursions and tastings. Take some time away from the trail and explore the local culture: Winery Visits, Cooking Class, Cheese Tastings and more...
Via Romea Sanese
Starting in the Middle Ages, Via Romea Sanese was the ancient pathway that connected Florence to Siena, two medieval cities who were in perpetual conflict.
It traverses what is now the renowned Chianti Wine Region and follows along part of what is an even older path of the prehistoric Estruscan civilization.
Traveled originally by merchants, soldiers, and pilgrims who were heading south to Rome, it was an alternate route to the famous Francigena road.
Historical highlights of the trail include the home where Nicolo’ Machiavelli wrote his famous work, “The Prince” while in exile by the Medici Family, The Benedictine Abbey of San Michele Arcangelo, Badia a Passingnano, and Castellina in Chianti.